Methanesulfonic Acid → HCID 69206894, compound

HRID 30656Notes

Reaction equation

HRID 30656 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([NH:12][NH2:13])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:16]S(O)(=O)=O.C(OCC)(OCC)OCC.O1CCCC1>O>[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]2[O:11][CH:16]=[N:13][N:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 8028TetrahydrofuranHCID 31214Ethyl orthoformateHCID 156556Acetic acid, (4-nitrophenoxy)-, hydrazide

Product 1

HCID 69206894HCID 69206894, compoundYield 343.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(4-nitrophenoxy)acetohydrazide (1.10 g), methanesulfonic acid (0.10 g), triethyl orthoformate (2.31 g) and tetrahydrofuran (50 mL) was heated under reflux for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 2-[(4-nitrophenoxy)methyl]-1,3,4-oxadiazole as colorless crystals (0.79 g, yield 69%) from a fraction eluted with hexane-ethyl acetate (1:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 125-126° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0b1a1b1a56b54aa8b12a6bb07c40b606
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

Loading…